Jackie’s Amalfi sunglasses, Carolyn’s slip dresses, Caroline’s tennis whites — three generations of warm-weather dressing that still sets the standard.
No American family has held the public’s attention the way the Kennedys have. The comparison to royalty gets made often, and not without reason: the political weight is one part of it, but the cultural pull is the part that has outlasted the presidencies. The women of the family carry a good deal of that. They remain the subject of bestselling biographies and prestige television, and the surname alone now works as a shorthand for an entire look.
Their influence, of course, reaches well past what they wore. Philanthropy, diplomacy, decades of public service. But their wardrobes were never accidental either, and because the family more or less drafted the template for Northeastern prep, Kennedy summer style resurfaces on every moodboard the moment the weather turns and the boats go back in the water.
Working through several decades of photographs and across the branches of the family tree, we’ve pulled together the most memorable of those looks. Jackie appears more than once, naturally — the Capri excursions, the Hyannis Port holidays. Carolyn Bessette-Kennedy’s ’90s silhouettes are here, the ones that go viral again every few months. So are Caroline’s preppy ensembles. And keep an eye out for a portrait of the family matriarch on her 92nd birthday, framed by pink summer blooms.
Twenty-one looks worth stealing from, below.
The Looks
1. Caroline Kennedy playing tennis in Central Park.
2. Jacqueline Kennedy Onassis walking a crowded street in Capri, Italy, in the early 1970s.
3. Rose Fitzgerald Kennedy photographed on her 92nd birthday at home in Hyannis Port, Massachusetts, 22 July 1982.
4. Jacqueline Bouvier and Eunice Kennedy at the Kennedy compound, June 1953.
5. Jacqueline Kennedy Onassis climbing the steps of the Acropolis in Athens.
6. Carolyn Bessette-Kennedy in a floral dress in New York City.
7. Joan Kennedy and Jackie Kennedy Onassis at the RFK Pro-Celebrity Tennis Tournament in New York City.
8. Ethel Kennedy and Robert F Kennedy sitting outdoors.
9. Caroline Kennedy at Michael Kennedy’s Harvard graduation.
10. Joan Kennedy with Ted Kennedy Jr at the RFK Tennis Tournament, 1974.
11. Carolyn Bessette-Kennedy out in New York City.
12. Jackie Kennedy on the pier at Amalfi, heading to Conca dei Marini beach by motorboat.
13. Joan and Ted Kennedy in New York City, circa 1980.
14. Caroline Kennedy at Athens Airport, 1970.
15. Jacqueline Bouvier on holiday at the Kennedy compound in Hyannis Port, Massachusetts, June 1953.
16. Eunice Kennedy on the lawn of the Kennedy home.
17. Kerry Kennedy at the RFK Pro-Celebrity Tennis Tournament, 1981.
18. Kathleen Kennedy with John F Kennedy in Palm Beach, Florida.
19. Joan Bennett Kennedy on her way to the Democratic Convention, 1964.
20. Caroline Kennedy layering necklaces over a printed dress, 1975.
21. John F Kennedy and Jacqueline Kennedy at the water’s edge in Hyannis Port, Massachusetts.
